Portland (PDX) to Chicago (ORD), Jan 14, 2027: round trips from $337, one way from $181

Portland (PDX) to Chicago (ORD), Jan 14, 2027: round trips from $337, one way from $181 on Axel, checked Oct 29, 2026. Lowest published fares: $337 round trip, Axel-exclusive, Alaska Airlines, 1 stop, Jan 14–15, 2027; $181 one way, Axel-exclusive, Alaska Airlines, nonstop, Jan 14, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $74 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $78 total · 5★ Sofitel Chicago Magnificent Mile, $214 total
• Hotels in Chicago for these nights (Jan 14–16, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ Warwick Allerton - Chicago, $180 total · 5★ Sofitel Chicago Magnificent Mile, $429 total
• Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $233 total · 4★ Warwick Allerton - Chicago, $276 total · 5★ Sofitel Chicago Magnificent Mile, $648 total
• Hotels in Chicago for these nights (Jan 14–18, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $308 total · 4★ Warwick Allerton - Chicago, $366 total · 5★ Sofitel Chicago Magnificent Mile, $871 total
• Hotels in Chicago for these nights (Jan 14–19, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $383 total · 4★ Warwick Allerton - Chicago, $458 total · 5★ Sofitel Chicago Magnificent Mile, $1,125 total
• Hotels in Chicago for these nights (Jan 14–20, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $458 total · 4★ Warwick Allerton - Chicago, $542 total · 5★ Sofitel Chicago Magnificent Mile, $1,378 total
• Hotels in Chicago for these nights (Jan 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ Warwick Allerton - Chicago, $627 total · 5★ Sofitel Chicago Magnificent Mile, $1,588 total
• Hotels in Chicago for these nights (Jan 14–22, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $626 total · 4★ Warwick Allerton - Chicago, $716 total · 5★ Sofitel Chicago Magnificent Mile, $1,824 total
• Hotels in Chicago for these nights (Jan 14–23, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $701 total · 4★ Warwick Allerton - Chicago, $816 total · 5★ Sofitel Chicago Magnificent Mile, $2,034 total
• Hotels in Chicago for these nights (Jan 14–24, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $776 total · 4★ Warwick Allerton - Chicago, $1,006 total · 5★ Sofitel Chicago Magnificent Mile, $2,621 total
• Hotels in Chicago for these nights (Jan 14–25, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $859 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $1,157 total · 5★ Nobu Hotel Chicago, $4,336 total
• Hotels in Chicago for these nights (Jan 14–26, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $934 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,392 total · 5★ Nobu Hotel Chicago, $4,769 total
• Hotels in Chicago for these nights (Jan 14–27, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,017 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,530 total · 5★ Nobu Hotel Chicago, $5,197 total
• Hotels in Chicago for these nights (Jan 14–28, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,092 total · 4★ Millennium Hotel Knickerbocker Chicago, $1,670 total · 5★ Nobu Hotel Chicago, $5,584 total

All hotels in Chicago

Route overview: Portland to Chicago (ORD) flight deals

2027-01-14 · one way · Axel-exclusive $180.50

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.

2027-01-14 · one way · Axel-exclusive $185.25

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.

2027-01-14 → 2027-01-15 · Axel-exclusive $337.25

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-15 15:19:00 → PDX 2027-01-15 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-15 15:19:00 → SEA 2027-01-15 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-15 19:54:00 → PDX 2027-01-15 20:50:00.

2027-01-14 → 2027-01-15 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-15 10:00:00 → PDX 2027-01-15 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-16 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-16 14:08:00 → PDX 2027-01-16 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-16 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-16 10:05:00 → PDX 2027-01-16 13:01:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-17 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-17 14:08:00 → PDX 2027-01-17 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-17 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-17 10:00:00 → PDX 2027-01-17 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-18 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-18 14:08:00 → PDX 2027-01-18 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-18 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-18 10:00:00 → PDX 2027-01-18 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-20 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-20 14:07:00 → PDX 2027-01-20 16:50:00; nonstop; 283 minutes. Local airport times.

2027-01-14 → 2027-01-20 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA562: ORD 2027-01-20 09:45:00 → PDX 2027-01-20 12:37:00; nonstop; 292 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $337.25

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA3186 / AS3430: ORD 2027-01-21 08:10:00 → PDX 2027-01-21 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2027-01-21 08:10:00 → SLC 2027-01-21 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2027-01-21 12:32:00 → PDX 2027-01-21 13:48:00.

2027-01-14 → 2027-01-21 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-21 14:08:00 → PDX 2027-01-21 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-22 · Axel-exclusive $337.25

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS407 / AS2239: ORD 2027-01-22 15:19:00 → PDX 2027-01-22 20:50:00; 1 stop(s) via SEA; 451 minutes. Local airport times.
  • AS407: ORD 2027-01-22 15:19:00 → SEA 2027-01-22 18:11:00; layover at SEA: 103 minutes.
  • AS2239: SEA 2027-01-22 19:54:00 → PDX 2027-01-22 20:50:00.

2027-01-14 → 2027-01-22 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-22 10:00:00 → PDX 2027-01-22 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-24 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-24 14:08:00 → PDX 2027-01-24 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-24 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-24 10:00:00 → PDX 2027-01-24 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-25 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-25 14:08:00 → PDX 2027-01-25 16:58:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-25 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA563: ORD 2027-01-25 10:00:00 → PDX 2027-01-25 12:56:00; nonstop; 296 minutes. Local airport times.

2027-01-14 → 2027-01-26 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-26 14:08:00 → PDX 2027-01-26 17:05:00; nonstop; 297 minutes. Local airport times.

2027-01-14 → 2027-01-26 · Axel-exclusive $351.50

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA2878: ORD 2027-01-26 17:05:00 → PDX 2027-01-26 19:55:00; nonstop; 290 minutes. Local airport times.

2027-01-14 → 2027-01-28 · Axel-exclusive $337.25

• American Airlines AA562: PDX 2027-01-14 13:30:00 → ORD 2027-01-14 19:44:00; nonstop; 254 minutes. Local airport times.
• American Airlines AA3186 / AS3430: ORD 2027-01-28 08:10:00 → PDX 2027-01-28 13:48:00; 1 stop(s) via SLC; 458 minutes. Local airport times.
  • AA3186: ORD 2027-01-28 08:10:00 → SLC 2027-01-28 10:56:00; layover at SLC: 96 minutes.
  • AS3430: SLC 2027-01-28 12:32:00 → PDX 2027-01-28 13:48:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $342.00

• Alaska Airlines AS324: PDX 2027-01-14 07:00:00 → ORD 2027-01-14 13:13:00; nonstop; 253 minutes. Local airport times.
• Alaska Airlines AS325: ORD 2027-01-28 14:08:00 → PDX 2027-01-28 17:05:00; nonstop; 297 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 13, 2027 · Return options
• Jan 15, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Portland (PDX) to Chicago (ORD) · Jan 14, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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